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一种过渡金属催化与光促进相结合的过程:由1,7-二芳基-1,6-二炔合成2,3-稠合的4-苯基萘-1-基羧酸酯

A Combined Transition-Metal-Catalyzed and Photopromoted Process: Synthesis of 2,3-Fused 4-Phenylnaphthalen-1-yl Carboxylates from 1,7-Diaryl-1,6-diynes.

作者信息

Yamamoto Yoshihiko, Mori Shota, Shibuya Masatoshi

机构信息

Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601 (Japan).

出版信息

Chemistry. 2015 Jun 15;21(25):9093-100. doi: 10.1002/chem.201500978. Epub 2015 May 15.

DOI:10.1002/chem.201500978
PMID:25980465
Abstract

2,3-Fused 4-phenylnaphthalen-1-yl carboxylates were synthesized in a step- and atom-economical manner using a ruthenium-catalyzed hydrocarboxylative cyclization of 1,7-diaryl-1,6-diynes and subsequent oxidative photocyclization. The scope of this novel two-step process was demonstrated by the construction of diverse structures from substrates with various tethers and terminal aryl groups. Late-stage CH functionalizations of the arylnaphthalene product further enhance the synthetic potential of the developed process.

摘要

以钌催化的1,7-二芳基-1,6-二炔的氢羧基化环化反应及随后的氧化光环化反应,以逐步且原子经济的方式合成了2,3-稠合的4-苯基萘-1-基羧酸酯。通过由具有各种连接基和末端芳基的底物构建多样结构,证明了这种新颖的两步法的适用范围。芳基萘产物的后期C-H官能化进一步提高了所开发方法的合成潜力。

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